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I believe the expiration starts from the first boot, which means that since you already booted to configure WinRM and install chocolatey and Puppet, the base box has already an expiration date set, and recreating a virtual machine from the base box will not reset the expiration date.

Yeah I realized this yesterday when I built one of them from the cloud box and saw the license countdown ticking down.

Regardless it's trivial for me to redo these every 60 days. I'll just take on the responsibility of repackaging from the source material and increment the vagrant cloud version. That way anyone uses them gets fresh copies every 60 days.